Preparation of o-iminooxymethylbenzoic acid

ABSTRACT

o-Iminooxymethylbenozic acids of the general formula I ##STR1## are disclosed where, m, X, R 1  and R 2  are defined herein.

This is a Division of application Ser. No. 08/041,848 filed on Apr. 2, 1993, U.S. Pat. No. 5,393,920.

The present invention relates to a novel process for preparing an o-iminooxymethylbenzoic acid of the general formula I ##STR2## where m is an integer from 0 to 3,

X is unbranched or branched C₁ -C₄ -alkyl; unbranched or branched C₁ -C₄ -alkoxy, nitro, cyano or halogen,

R¹ and R² are identical or different and each is hydrogen, cyano, hydroxyl, unbranched or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₅ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, benzylamino, C₁ -C₄ -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted aryl-C₂ -C₄ -alkenyl, unsubstituted or substituted aryloxy-C₁ -C.sub. 4 -alkyl, unsubstituted or substituted arylthio-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted heteroaryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl, unsubstituted or substituted hetaryloxy-C₁ -C₄ -alkyl, hetarylthio-C₁ -C₄ -alkyl, unsubstituted or substituted heterocyclyl, or unsubstituted or substituted heterocyclyloxy or

N(R₆)₂ where the meanings of the two R⁶ radicals are identical or different and are H, C₁ -C₆ -alkyl, or unsubstituted or substituted phenyl, or

--CO--N(R⁷)₂, where the meanings of the two R⁷ radicals are identical or different and are H, C₁ -C₄ -alkyl or unsubstituted or substituted phenyl,

where unsubstituted or substituted includes, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C₃ -C₆ -cycloalkyl, heterocyclyl or heterocyclyloxy, or

R¹ and R², together with the C atom whose substituents they are, form a carbocyclic or heterocyclic ring which can be substituted by the radicals mentioned above under unsubstituted or substituted or

R¹ or R² is halogen or the group ##STR3## is the radical ##STR4## where n is the integers from 1 to 4,

the radicals R⁸ are identical or different and each is H, halogen, cyano, nitro, unsubstituted or substituted C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy, by reacting an oxime of the general formula II ##STR5## where R¹ and R² have the abovementioned meanings, with a lactone of the general formula III ##STR6## where X and m have the abovementioned meanings, if appropriate in the presence of a base or of a diluent or of a mixture thereof.

o-Iminooxymethylbenzoic acids are described in EP 234,045 (p. 97). The synthesis there starts from benzyl bromide i, which can be prepared in turn from methyl o-methylbenzoate by bromination according to methods known per se (see Organikum, p. 212) and which is then reacted with the salt of an oxime (EP 234,045, p. 97). In the last step, the ester group is hydrolyzed in the customary manner to liberate the acid. ##STR7##

The preparation and reaction of the benzyl bromide i are particularly a problem. In particular on the large scale, working with bromine or N-bromosuccinimide is complicated and troublesome. Bromine-containing waste products furthermore have to be disposed of.

This method of preparation has the crucial disadvantage of being a long and multi-step process. The yields, in particular the space-time yield, are poor. As a result of this, the preparation of the intermediates of the formula I by the known process is very troublesome, undesired waste products being produced.

It is an object of the present invention to prepare the compounds I in an industrially more practicable way.

We have found that this object is achieved by the process described above.

The invention further relates to a process for preparing an o-iminooxymethylbenzoic acid I, wherein

a) an oxime of the general formula II ##STR8## is converted into the corresponding salt by means of a base in the presence of a diluent,

b) this salt is mixed with a lactone of the general formula III ##STR9## and c) the mixture is further reacted in solution at from 20° to 250° C., or

d) the diluent is distilled off and the mixture is reacted in the molten state at from 50° to 250° C.

Useful bases are in particular alkali metal hydroxides such as sodium hydroxide and potassium hydroxide and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide and potassium methoxide and metal hydrides such as sodium hydride; the alkali metal alkoxides and the metal hydrides are particularly preferred.

As a rule, process step (a) is carried out in the presence of a solvent or diluent, the reaction temperature normally being from 0° to 100° C., preferably from 20° to 80° C.

Suitable solvents or diluents are aromatic hydrocarbons such as benzene, toluene and o-, m- or p-xylene, alcohols such as methanol, ethanol and isopropanol, ethers such as dimethoxyethane or tetrahydrofuran, or liquids such as acetonitrile, dimethylformamide, N-methylpyrrolidone, dimethylpropyleneurea or mixtures of said solvents. Methanol and ethanol, dimethylformamide and N-methylpyrrolidone are particularly preferred.

The amount of base is not critical. For complete conversion of the oxime II to the corresponding salt (oximate) at least equimolar amounts of base are required; preferably an excess of 1 to 6 mol % of base are used, based on the amount of lactone III.

The salts of the oxime (oximate) II are advantageously mixed with the lactones of the formula III without isolation from the reaction mixture and fused together with simultaneous removal of the solvent or further reacted in the diluent.

In general, process step (d) is carried out at from 50° to 250° C., preferably from 160° to 200° C. In this process, with a decreasing amount of diluent the lactone III is converted from the dissolved to the liquid state and a readily miscible solution of the oximate in the lactone III is obtained.

Process step (c) is carried out at from 50° to 200° C., preferably from 60° to 160° C.

Normally, the oximate and lactone are employed in an approximately stoichiometric ratio, but in some cases an excess of one or the other component, for example up to 10 mol %, may be advisable.

In process steps (a) to (d), no particular conditions with respect to the pressure are necessary; the process is therefore expediently carried out at atmospheric pressure.

After the reaction has ended, the reaction mixture or the melt is diluted with water. The solution obtained is acidified, preferably with an inorganic acid such as hydrochloric acid or sulfuric acid, to liberate the o-iminooxymethylbenzoic acid I. Further working-up is carried out in the customary manner.

The compounds of the formula I prepared by the process according to the invention can basically be obtained as E/Z mixtures with respect to the C=N double bond if R¹ and R² are different. As a rule, however, far more predominantly, if not exclusively, only one isomer is obtained if R¹ and R² are sterically sufficiently different.

The process according to the invention can be carried out either batchwise or continuously. In the continuous procedure, the reactants are passed, for example, through a tubular reactor or over stirring vessel cascades.

The preparation method described can be used successfully for the synthesis of the o-iminooxymethylbenzoic acids of the formula I defined, in particular for those compounds in which the substituents R¹, R², X and m have the following meanings:

m is an integer from 0 to 2 (in particular 0 or 1).

X is methyl, ethyl, isopropyl, methoxy, nitro, cyano, fluorine, chlorine or bromine.

R¹ is hydrogen; cyano; C₁ -C₆ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl or butyl); C₃ -C₆ -cycloalkyl (in particular cyclopropyl); C₁ -C₄ -alkylthio (in particular methylthio, ethylthio, n-propylthio or isopropylthio); C₁ -C₄ -alkyl thioalkyl (in particular methylthiomethylene); arylthioalkyl (in particular phenylthiomethylene); C₁ -C₄ -alkoxy(in particular methoxy, ethoxy, n-propoxy or isopropoxy); C₁ -C₄ -alkoxyalkyl (in particular methoxymethylene or ethoxymethylene); aryloxyalkyl (in particular phenoxymethylene); C₁ -C₄ -alkylamino (in particular methylamino, ethylamino, n-propylamino or isopropylamino); C₁ -C₃ -dialkylamino (in particular dimethylamino or diethylamino); benzylamino; benzylthio; benzyloxy; benzyl; vinyl; E-chlorovinyl; E-bromovinyl; --OH; NH₂ ; --CO--NHCH₃ ; --CONHEt; --CONHnPr; --CONHiPr; --CON(CH₃)₂ ; --CON(Et)₂ ; --COOCH₃ ; --COOEt; --COOnPr; or --COOiPr.

R² is C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, i-propyl or n-butyl); phenyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkoxy (in particular methoxy, ethoxy or i-propoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); fluorine; chlorine; bromine; iodine; C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl); C₃ -C₆ -cycloalkyl (in particular cyclopropyl, cyclopentyl or cyclohexyl); nitro; cyano; trifluoromethyl; trichloromethyl; phenyl; phenoxy; benzyl; benzyloxy; hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl or isoxazolyl); heterocyclyl (in particular morpholinyl, pyrrolidinyl, thiomorpholinyl, piperidinyl, piperazinyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydropyranyl or tetrahydrothiopyranyl); hetaryloxy (in particular pyridinyloxy, pyrimidinyloxy, pyrazinyloxy or pyridazinyloxy); C₁ -C₄ -alkylcarbonyl (in particular --COMe, --COEt, --COnPr, --COiPr, --COnBu or --CO tert-Bu); C₁ -C₄ -alkoxycarbonyl (in particular --COOMe, --COOEt, --COOnPr, --COOiPr, --COOnBu or --COO tert-Bu); C₁ -C₄ -alkylaminocarbonyl (in particular --CONHMe, --CONHEt, --CONHPr, --CONHiPr, --CONHnBu, --CONH tert-Bu); C₁ -C₄ -dialkylaminocarbonyl (in particular --CON(Me)₂, -CON(Et)₂); or C₁ -C₄ -dialkylamino (in particular --N(Me)2.sub., --N(Et)₂); Ph(Me)N--; Ph(Et)N--; --SO₂ Me; --SO₂ Et; --SOMe; --SOEt; --SO₂ N(Me)₂ ; --SO₂ N(Et)₂ ; --C(Me)═N--OMe; --C(Me)═N--OEt; --C(Me)═N--OnPr; --C(Me)═N--OiPr; --C(Me)═N--OnBu; --C(Me)═N--OtertBu; --C(Me)═N--Obenzyl; --C(Et)═N--OMe; --C(Et)═N--OEt; --C(Et)═N--OnPr; --C(Et)═N--OiPr; --C(Et)═N--OnBu; --C(Et)═N--OtertBu; --C(Et)═N--Obenzyl; --C(nPr)═N--OMe; --C(nPr)═N--OEt; --C(npr)═N--OnPr; --C(NPr)═N--OiPr; --C(nPr)═N--OnBu; --C(nPr)═N--OtertBu; --C(nPr)═N--Obenzyl; --C(iPr)═N--OMe; --C(iPr)═N--OEt; --C(iPr)═OnPr; --C(iPr)═N--OiPr; --C(iPr)═N--OnBu; --C(iPr)═N--OtertBu; --C(iPr)═N--Obenzyl];

naphthyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl or isopropyl); C₁ -C₄ -alkoxy (in particular methoxy, ethoxy, n-propoxyor isopropoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); or F, Cl, Br, NO₂ or CN];

hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, quinoxalyl, naphthyridinyl, trizolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl, benzothienyl, benzofuryl, indolyl, benzimidazolyl, benzopyrazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl or benzisoxazolyl) where the hetaryl can be substituted by 0 to 2 substituents, selected from methyl, ethyl, i-propyl, n-propyl, n-butyl, tert-butyl, cyclopropyl, F, Cl, Br, I, methoxy, ethoxy, n-propoxy, i-propoxy, cyano, nitro, COOMe, COOEt, COOnPr, COOiPr, CONHMe, CONHEt, CON(Me)₂, CON(Et)₂, methylthio, ethylthio, --COCH₃, --COEt, --COiPr, --COnPr, phenyl and phenoxy;

phenylcarbonyl [where the phenyl ring can be substituted by 0 to 3 substituents, selected from: methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, cyclopropyl, MeO, EtO, nPrO, iPrO, MeS, EtS, F, Cl, Br, I, NO₂, cyano or trifluoromethyl] or the radical ##STR10## can have the following meanings ##STR11##

The o-iminooxymethylbenzoic acids of the formula I are surprisingly obtained in high yield and excellent purity by the process according to the invention. This was not to be expected from the prior art. In particular, it was in no case to be foreseen that the salt of the oxime (oximate) could be reacted readily in this reaction at high temperatures (100°-160° C.) without decomposing. Compared to the prior art, the process according to the invention has a number of advantages. It can be carried out in a very simple manner on the industrial scale. It does not require the use of bromine or possibly chlorine or N-bromosuccinimide or N-chlorosuccinimide. It thus avoids the formation of halogen-containing waste products and is therefore industrially simpler and fairly problem-free. Corrosion problems due to halogen are additionally avoided. A significant advantage of this process is furthermore that it leads to the acids of the formula I in a one-step, industrially simple and problem-free process.

A further advantage is that in one variant of the process the alkali metal oximate produced as an intermediate does not have to be isolated as a solid, but that a fluid transition from a solution or suspension of the oximate from the diluent to the melt (oximate+ lactone III) takes place. This is achieved by adding the lactone III to the salt of the oxime II in the presence of a diluent and then distilling off the diluent.

In another variant, the oximate can be further reacted with the phthalide in a solvent. The flexibility of the reaction procedure in the context indicated enables the optimum conditions to be selected for the particular individual case.

The o-iminooxymethylbenzoic acids I are useful intermediates for preparing o-iminooxymethylphenyl esters IX and X, which are used in plant protection, in particular as fungicides [cf. EP-A 370,629; EP-A 414,155; EP-A 426,460; EP-A 460,575; WO 70/07493). ##STR12##

In the following reaction scheme, two particularly preferred synthetic routes for preparing the compounds IX from o-iminooxymethylbenzoic acid are shown: ##STR13##

The benzoic acids I are advantageously converted into their acid chlorides by this process (cf. Organikum, VEB Deutscher Verlag der Wissenschaften, 16th edition, Berlin, 1986, page 423 et seq.) and the corresponding benzoyl cyanides VI are prepared from these, using an aqueous organic two-phase system and in the presence of a phase-transfer catalyst [Tetrahedron Letters (1974) 2275].

The benzoyl cyanides IV are then reacted with lower alcohols by the Pinner reaction [cf. Angew. Chemie 94 (1982) 1], phenylglyoxylic acid ester VIII resulting. The α-ketoesters VIII are then reacted either with o-methylhydroxylamine (or a salt thereof) to obtain the bisoxime ether of the type X, or reacted with a methoxymethylenation reagent such as methoxymethylenetriphenylphosphorane (cf. EP 0,044,448, Jul. 4, 1980) to prepare the acrylic esters IX. In a second known process, the acid I is first converted into its corresponding esters V (cf. Organikum page 499). These esters V are then converted to the β-ketosulfoxide VII in the presence of base and dimethyl sulfoxide (J. Am. Chem. Soc. 88 (1966) 5498). The α-ketoesters VIII are then obtained by the Pummerer reaction by bromination of the compound VII in the presence of a base and rearrangement in an acid (cf. J. Am. Chem. Soc. 88 (1966) 5498 and Synthesis (1982) 41).

For the intermediates I, IV, V, VI and VII, the radicals R¹, R², X and m preferably have the following meanings:

m is an integer from 0 to 2 (in particular 0 or 1)

X is methyl, ethyl, isopropyl, methoxy, nitro, cyano, fluorine, chlorine or bromine.

R¹ is hydrogen; cyano; C₁ -C₆ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl or butyl); C₃ -C₆ -cycloalkyl (in particular cyclopropyl); C₁ -C₄ -alkylthio (in particular methylthio, ethylthio, n-propylthio or isopropylthio); C₁ -C₄ -alkylthioalkyl (in particular methylthiomethylene); arylthioalkyl (in particular phenylthiomethylene); C₁ -C₄ -alkoxy (in particular methoxy, ethoxy, n-propoxy or isopropoxy); C₁ -C₄ -alkoxyalkyl (in particular methoxymethylene or ethoxymethylene); aryloxyalkyl (in particular phenoxymethylene); C₁ -C₄ -alkylamino (in particular methylamino, ethylamino, n-propylamino or isopropylamino); C₁ -C₃ -dialkylamino (in particular dimethylamino or diethylamino); benzylamino; benzylthio; benzyloxy; benzyl; vinyl; E-chlorovinyl; E-bromovinyl; --OH; NH₂ ; --CO--NHCH₃ ; --CONHEt; --CONHnPr; --CONHiPr; --CON(CH₃)₂ ; --CON(Et)₂ ; --COOCH₃ ; --COOEt; --COOnPr; or --COOiPr.

R² is C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, i-propyl or n-butyl); phenyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkoxy (in particular methoxy, ethoxy or i-propoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); fluorine; chlorine; bromine; iodine; C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl); C₃ -C₆ -cycloalkyl (in particular cyclopropyl, cyclopentyl or cyclohexyl); nitro; cyano; trifluoromethyl; trichloromethyl; phenyl; phenoxy; benzyl; benzyloxy; hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl or isoxazolyl); heterocyclyl (in particular morpholinyl, pyrrolidinyl, thiomorpholinyl, piperidinyl, piperazinyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydropyranyl or tetrahydrothiopyranyl); hetaryloxy (in particular pyridinyloxy, pyrimidinyloxy, pyrazinyloxy or pyridazinyloxy); C₁ -C₄ -alkylcarbonyl (in particular --COMe, --COEt, --COnPr, --COiPr, --COnBu or --CO tert-Bu); C₁ -C₄ -alkoxycarbonyl (in particular --COOMe, --COOEt, --COOnPr, --COOiPr, --COOnBu or --COO tert-Bu); C₁ -C₄ -alkylaminocarbonyl (in particular --CONHMe, --CONHEt, --CONHPr, --CONHiPr, --CONHnBu, --CONH tert-Bu); C₁ -C₄ -dialkylaminocarbonyl (in particular --CON(Me)₂, --CON(Et)₂); or C₁ -C₄ -dialkylamino (in particular --N(Me)₂, --N(ET)₂); Ph(Me)N--; Ph(Et)N--; --SO₂ Me; --SO₂ Et; --SOMe; --SOEt; --SO₂ N(Me)₂ ; --SO₂ N(Et)₂ ; --C(Me)═N--OMe; --C(Me)═N--OEt --C(Me)═N--OnPr; --C(Me)═N--OiPr; --C(Me)═N--OnBu; --C(Me)═N--OtertBu; --C(Me)═N--Obenzyl; --C(Et)═N--OMe; --C(Et)═N--OEt; --C(Et)═N--OnPr; --C(Et)═N--OiPr; ═C(Et)═N--OnBu; --C(Et)═N--OtertBu; --C(Et)═N--Obenzyl; --C(nPr)═N--OMe; --C(nPr)═N--OEt; --C(nPr)═N--OnPr; --C(NPr)═N--OiPr --C(nPr)═N--OnBu; --C(nPr)═N--OtertBu; --C(nPr)═N--Obenzyl; --C(iPr)═N--OMe; --C(iPr)═N--OEt; --C(iPr)═OnPr; --C(iPr)═N--OiPr; --C(iPr)═N--OnBu; --C(iPr)═N--OtertBu; --C(iPr)═N--Obenzyl];

naphthyl [unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkyl (in particular methyl, ethyl, n-propyl or isopropyl); C₁ -C₄ -alkoxy (in particular methoxy, ethoxy, n-propoxyor isopropoxy); C₁ -C₄ -alkylthio (in particular methylthio or ethylthio); or F, Cl, Br, NO₂ or CN];

hetaryl (in particular pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, quinoxalyl, naphthyridinyl, trizolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl, benzothienyl, benzofuryl, indolyl, benzimidazolyl, benzopyrazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl or benzisoxazolyl) where the heteroaromatic can be substituted by 0 to 2 substituents, selected from methyl, ethyl, i-propyl, n-propyl, n-butyl, tert-butyl, cyclopropyl, F, Cl, Br, I, methoxy, ethoxy, n-propoxy, i-propoxy, cyano, nitro, COOMe, COOEr, COOnPr, COOiPr, CONHMe, CONHEt, CON(Me)₂, CON(Et)₂, methylthio, ethylthio, --COCH₃, --COEt, --COiPr, --COnPr, phenyl and phenoxy; phenylcarbonyl [where the phenyl ring can be substituted by 0 to 3 substituents, selected from: methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, cyclopropyl, MeO, EtO, nPrO, iPrO, MeS, EtS, F, Cl, Br, I, NO₂, cyano or trifluoromethyl] or the radical ##STR14## can have the following meanings ##STR15##

For the intermediate VIII, R⁴ and R⁵ preferably have the following meanings:

R⁴ is benzyl; C₁ -C₄ -alkylcarbonyl (e.g. --COMe, --COEt, --COnPr, --COiPr, --COnBu, --COtertBu); C₁ -C₄ -alkoxycarbonyl (e.g. --COOMe, --COOEt, --COOnPr, --COOiPr, --COOnBu, --COOiBu, --COOtertBu); phenyl; naphthyl; pyridinyl; pyrimidinyl; pyrazinyl; pyridazinyl; triazinyl; quinolyl; quinoxalyl; naphthyridinyl; triazolyl; imidazolyl; pyrazolyl; thiazolyl; isothiazolyl; oxazolyl; isoxazolyl; oxadiazolyl; thiadiazolyl; thienyl; furyl; pyrrolyl; benzothienyl; benzofuryl; indolyl; benzimidazolyl; benzopyrazolyl; benzothiazolyl; benzisothiazolyl; benzoxazolyl; or benzisoxazolyl; it being possible for any aromatic or heteroaromatic ring to be substituted by 1 to 3 groups selected from: hydrogen; F; Cl; Br; I; nitro; cyano; C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl); C₁ -C₄ -alkoxy (e.g. methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, tert-butoxy); trifluoromethyl; trichloromethyl; phenyl; phenoxy; or benzyloxy.

R⁵ is hydrogen; C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl); C₁ -C₄ -alkylcarbonyl (e.g. --COMe, --COEt, --COnPr, --COiPr, --COnBu, --COiBu, --COtert--Bu); C₁ -C₄ -alkoxycarbonyl (e.g. --COOMe, --COOEt, --COOnPr, --COOiPrn, --COOnBu, --COOiBu, --COO-tertBu); cyano; C₁ -C₄ -alkylthio ( e.g. --SMe, --SEt, --SnPr, --SiPr, --SnBu, --SiBu, --StertBu); C₁ -C₄ -alkoxy (e.g. --OMe, --OEt, --OnPr, OiPr, --OnBu, --OiBu, --OtertBu); C₃ -C₆ -cycloalkyl (e.g. cyclopropyl ); NR⁹ R¹⁰.

R⁹ is C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl, i-propyl ); phenyl C₁ -C₄ -alkyl (e.g. benzyl, 2-phenylethyl, 1-phenylethyl); or phenyl.

R¹⁰ is hydrogen; C₁ -C₄ -alkyl (e.g. methyl, ethyl, n-propyl or i-propyl) or the radical ##STR16## has the following meanings:

The Examples illustrate the invention.

EXAMPLE 1

Compound 32 in Table 1

25.4 g (0.15 mol) of p-chloroacetophenone oxime are dissolved in 150 ml of methanol using 27 g of a 30% strength (% by weight) sodium methoxide solution, the mixture is heated under reflux for 30 min, the methanol is distilled off, 20 g (0.15 mol) of phthalide are added and the mixture is heated at 180° C. for 2 hours. The heating is removed, 250 ml of water are cautiously added at 100° C., the mixture is extracted twice with methyl tert-butyl ether (MTBE) after cooling to 20° C., the aqueous phase is acidified to pH 2 with conc. H₂ SO₄ and the precipitated solid is filtered off with suction. 25.9 g (57%) of crude acid are obtained. Warning: In the form of pure substances, the sodium salts of acetophenone oximes can decompose violently above 150° C. The following process variants (Examples 2 to 5) are therefore recommended for the reaction.

EXAMPLE 2

Compound 31 in Table 1

7.5 g (0.05 mol) of p-methylacetophenone oxime are dissolved in 30 ml of CH₃ OH under nitrogen gas using 9 g of a 30% strength sodium methoxide solution, the mixture is refluxed for 1 hour, 6.7 g (0.05 mol) of phthalide are added, the methanol is distilled off and the mixture is heated at 160° C. for 2 hours. After cooling to 20° C., 100 ml of water are added, the mixture is extracted twice with MTBE, and the aqueous phase is acidified to pH 2 with conc. H₂ SO₄. The dark precipitated material is separated from the water and dissolved in MTBE, and the solution is dried and concentrated. 9.6 g (68 %) of crude acid are obtained.

EXAMPLE 3

Compound 31 in Table 1

2.6 g of NaH (55% strength) are introduced, 7.5 g (0.05 mol) of p-methylacetophenone oxime are dissolved in 50 ml of tetrahydrofuran (THF), added dropwise under nitrogen gas, and the mixture is heated at 60° C. for 1 hour, 50 ml of THF are added and it is cooled to 40° C. A solution of 6.7 g (0.05 mol) of phthalide in 30 ml of THF is added, the solvent is distilled off and the mixture is heated at 160° C. for 2 hours. After cooling, 100 ml of H₂ O are added, the mixture is extracted twice with MTBE, the aqueous phase is acidified to pH 2 with conc. H₂ SO₄, the suspension is stirred with a little pentane, and the precipitate is filtered off with suction and washed with water. After drying in a vacuum drying oven 7.4 g (52 %) of crude acid are obtained.

EXAMPLE 4

Compound 31 in Table 1

2.6 g of NaH (55% strength) are introduced, 7.5 g (0.05 mol) of p-methylacetophenone oxime are added dropwise in 50 ml of dimethylformamide (DMF) under N₂, the mixture is stirred at 60° C. for a further hour, 50 ml of DMF are added dropwise and the suspension is refluxed for 2 hours. After cooling, 200 ml of H₂₀ are added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with H₂ O and dried in a vacuum drying oven. 9.3 g (66%) of acid are obtained.

EXAMPLE 5

Compound 31 in Table 1

2.6 g of NaH (55% strength) are introduced, 7.5 g (0.05 mol) of p-methylacetophenone oxime are added dropwise in 50 ml of DMF under N₂, the mixture is stirred at 60° C. for a further hour and 50 ml of DMF are added, 6.7 g (0.05 mol) of phthalide in 50 ml of DMF are added dropwise, and the suspension is stirred at 100° C. for 6 hours and at 20° C. overnight. Water (200 ml) is then added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with water and dried. 10.2 g (72%) of pale crystals of the acid are obtained. M.p.=152° C.

EXAMPLE 6

Compound 31 in Table 5

4 g (0.016 mol) of the acid (compound no. 31, Table 1) are dissolved in 20 ml of methanol, 2.5 g (0.028 mol) of SOCl₂ are added dropwise and the reaction mixture is refluxed for 1 hour. The solvent is evaporated on a rotary evaporator, the residue is dissolved in MTBE, the solution is washed with 10% strength Na₂ CO₃ solution and dried with Na₂ SO₄ and the solvent is evaporated. 3.4 g (82%) of oil are obtained.

EXAMPLE 7

Compound 32 in Table 5

12.5 g (0.041 mol) of the acid (compound 32 in Table 1) are dissolved in 50 ml of methanol, 7.4 g (0.083 mol) of SOCl₂ are added dropwise and the reaction mixture is refluxed for 2 hours. The solvent is evaporated on the rotary evaporator, the residue is dissolved in MTBE, the solution is washed three times with a 10% strength aqueous Na₂ CO₃ solution and dried with Na₂ SO₄ and the solvent is evaporated. 11.2 g (86%) of oil are obtained.

The following o-iminooxymethylbenzoic acids of the formula I can be prepared, for example, by the processes mentioned.

EXAMPLE 8

Compound 31 in Table 1

45.8 g of NaH (55% strength) are suspended in 1000 ml of DMF, 149 g (1 mol) of p-methylacetophenone oxime are added dropwise in 600 ml of DMF under N₂, the mixture is stirred at 60° C. for a further hour, 200 ml of DMF are added, 134 g (1 mol) of phthalide in 500 ml of DMF are added dropwise, and the suspension is stirred at 100° C. for 6 hours and at 20° C. overnight. Water (about 5 l) is then added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with water and dried. 262 g (92%) of pale crystals of the acid are obtained. M.p.=152° C.

EXAMPLE 9

Compound 46 in Table 1

2.65 g of NaH (55% strength) are suspended in 50 ml of DMF, 7.05 g of 3-acetylthiophene oxime are added dropwise in 50 ml of DMF under N₂, the mixture is stirred at 60° C. for a further hour, 6.7 g of phthalide in 50 ml of DMF are added dropwise, and the suspension is stirred at 100° C. for 8 hours. After cooling, about 150 ml of H₂ O are added, the mixture is acidified with conc. H₂ SO₄, and the precipitate is filtered off with suction, washed with water and dried. 9 g (65%) of crystals of the acid are obtained. M.p.=149°-151° C.

EXAMPLE 10

Compound 31 in Table 6

1.75 g of DMSO are initially introduced into 5 ml of THF at -40° C., 25 g of butyllithium solution (1.6M) are added dropwise at -40° C. under N₂, the mixture is further stirred at 0° C. until outgassing ceases, compound 31 Tab. 5 in 15 ml of THF is added dropwise at -40° C. and the mixture is stirred at RT for 2 hours. The reaction mixture is hydrolyzed using an NH₄ Cl solution, acidified with 2N HCl and extracted with MTBE, and the organic phase is neutralized using solid Na₂ CO₃, dried and concentrated. After chromatographic separation, 2.9 g (42%) of compound 31 in Table 6 are obtained.

EXAMPLE 11

Compound 31 in Table 4

2.9 g of compound 31 in Table 6 are dissolved in 30 ml of acetone, 1.3 g of dibromodimethylhydantoin are added at RT, and the mixture is stirred at RT for a further 15 min and concentrated. The residue is dissolved in 40 ml of methanol, 2 ml of conc. HCl are added and stirring of the solution is continued at RT for 2 h. The reaction mixture is taken up in MTBE/water, and the organic phase is washed with Na₂ CO₃ and water, dried and concentrated. The product is chromatographed and 0.6 g of a mixture of p-methylacetophenone and compound 31 in Table 4 is obtained.

¹ H-NMR (CDCl₃ /TMS): 2.25 (s,3H); 2.35(s,3H); 3.90(s,3H); 5.55(s,2H); 7.05-7.80 (m,8H) ppm.

EXAMPLE 12

Compound 31 in Table 2

10 g of compound 31 in Table 1 are suspended in 80 ml of toluene, 8.3 g of pyridine and 2 drops of DMF are added, 6.25 g of SOCl₂ are added dropwise at 0° C., the cooling is removed and the mixture is stirred for a further 2 hours. The yellow precipitate is filtered off with suction and washed with toluene, and the mother liquor is concentrated. 5.3 g of crude product are obtained.

¹ H-NMR (CDCl₃ /TMS: 2.35 (s,6H); 5.70 (s,2H); 7.10-8.15 (m,8H) ppm.

EXAMPLE 13 Ethyl o-[1-(4-methylphenyl)ethyliminooxymethyl]phenylgloxylate

(Compound of type VIII where R₄ =4-methylphenyl; R₅ =methyl; R₁₁ =ethyl)

3.0 g of compound 31 in Table 6 are dissolved in 30 ml of acetone, 1.4 g of dibromodimethylhydantoin are added at RT, and the mixture is stirred at RT for a further 15 min and concentrated. The residue is dissolved in 40 ml of ethanol, 2 ml of conc. HCl are added and stirring of the solution is continued at RT for 4 hours. The reaction mixture is taken up in MTBE/water, and the organic phase is neutralized using Na₂ CO₃, dried and concentrated. The p-methylacetophenone formed is distilled in a bulb tube and the bottom is chromatographed. 0.4 g of ethyl o-[1-(4-methylphenyl)ethyliminooxymethyl]phenylglyoxylate is obtained.

¹ H-NMR (CDCl₃ /TMS): 1.35 (t,3H); 2.30 (s,3H); 2.35 (s,3H); 4.40 (q,2H); 5.55 (s,2H); 7.05-7.80 (m,8H) ppm.

IR: 1733; 1683; 1195; 1038; 1012 cm⁻¹.

The following o-iminooxymethylbenzoic acids of the formula I can be prepared, for example, by the processes mentioned.

                                      TABLE 1                                      __________________________________________________________________________      ##STR18##                          I                                          No. R.sup.1 R.sup.2          Data                                              __________________________________________________________________________     1   CN                                                                         2-naphthyl                                                                     2   CN                                                                         n-hexyl                                                                        3   CN                                                                         cyclohexyl                                                                     4   CN                                                                         thiophenyl                                                                     5   CN                                                                         phenyl                                                                         6   CN                                                                         4-Me-phenyl                                                                    7   CN                                                                         4-chlorophenyl                                                                 8   CN                                                                         4-tert-butyl                                                                   9   CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CN.sub.3                                                                   2-naphthyl                                                                     27  CN.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                        IR: 1678; 1318;                                                                                         1046; 820;                                                                     743 cm.sup.-1                                     32  CH.sub.3                                                                   4-chlorophenyl                                                                     IR: 1687; 1318;                                                                                         1042; 945;                                                                     733 cm.sup.-1                                     33  CH.sub.3                                                                   4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                          IR: 1677; 1320;                                                                                         1044; 780                                                                      738 cm.sup.-1                                     47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62   OCH.sub.3                                                                 2-fluorophenyl                                                                 63  OCH.sub.3                                                                  3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub.3                                                                  3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                 86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub. 3                                                                5-(4-methylthiazolyl)                                                          99  NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NOnBu                                                                    145                                                                                 ##STR19##                                                                 __________________________________________________________________________

The following o-iminooxymethylbenzoyl chlorides IV can be prepared by the processes mentioned.

                                      TABLE 2                                      __________________________________________________________________________      ##STR20##                            IV                                       No. R.sup.1 R.sup.2          Data                                              __________________________________________________________________________     1   CN                                                                         2-naphthyl                                                                     2   CN                                                                         n-hexyl                                                                        3   CN                                                                         cyclohexyl                                                                     4   CN                                                                         thiophenyl                                                                     5   CN                                                                         phenyl                                                                         6   CN                                                                         4-Me-phenyl                                                                    7   CN                                                                         4-chlorophenyl                                                                 8   CN                                                                         4-tert-butyl                                                                   9   CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CH.sub.3                                                                   2-naphthyl                                                                     27  CH.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                        NMR (CDCl.sub.3 /TMS)                                                                                   2.35(s, 6H); 5.70                                                              (s, 2H); 7.10-8.15                                                             (m, 8H)                                           32  CH.sub.3                                                                   4-chlorophenyl                                                                 33  CH.sub.3                                                                   4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                      47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62  OCH.sub.3                                                                  2-fluorophenyl                                                                 63  OCH.sub.3                                                                  3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub. 3 (CNOMe)-phenyl                                                     68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub.3                                                                  3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                 86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          99  NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NOnBu                                                                    145                                                                                 ##STR21##                                                                 __________________________________________________________________________

The following o-iminooxymethylbenzoyl cyanides VI can be prepared, for example, by the processes mentioned.

                                      TABLE 3                                      __________________________________________________________________________      ##STR22##                          VI                                         No. R.sup.1 R.sup.2          Data                                              __________________________________________________________________________     1   CN                                                                         2-naphthyl                                                                     2   CN                                                                         n-hexyl                                                                        3   CN                                                                         cyclohexyl                                                                     4   CN                                                                         thiophenyl                                                                     5   CN                                                                         phenyl                                                                         6   CN                                                                         4-Me-phenyl                                                                    7   CN                                                                         4-chlorophenyl                                                                 8   CN                                                                         4-tert-butyl                                                                   9   CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CH.sub.3                                                                   2-naphthyl                                                                     27  CH.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                    32  CH.sub.3                                                                   4-chlorophenyl                                                                 33  CH.sub. 3                                                                  4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-Phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                      47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62  OCH.sub.3                                                                  2-fluorophenyl                                                                 63  OCH.sub.3                                                                  3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub. 3                                                                 3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                 86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          99  NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub. 3                                                                 4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NOnBu                                                                    145                                                                                 ##STR23##                                                                 __________________________________________________________________________

The following methyl o-iminooxymethylphenylglyoxylates VIII can be prepared, for example, by the processes mentioned.

                                      TABLE 4                                      __________________________________________________________________________      ##STR24##                         VIII                                        No. R.sup.5 R.sup.4          Data                                              __________________________________________________________________________     1   CN                                                                         2-naphthyl                                                                     2   CN                                                                         n-hexyl                                                                        3   CN                                                                         cyclohexyl                                                                     4   CN                                                                         thiophenyl                                                                     5   CN                                                                         phenyl                                                                         6   CN                                                                         4-Me-phenyl                                                                    7   CN                                                                         4-chlorophenyl                                                                 8   CN                                                                         4-tert-butyl                                                                   9   CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CH.sub.3                                                                   2-naphthyl                                                                     27  CH.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                        IR: 1738; 1687;                                                                                         1206; 1011;                                                                    818 cm.sup.-1                                     32  CH.sub.3                                                                   4-chlorophenyl                                                                 33  CH.sub.3                                                                   4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                      47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62  OCH.sub.3                                                                  2-fluorophenyl                                                                 63  OCH.sub.3                                                                  3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub.3                                                                  3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                 86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          99  NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103  SCH.sub.3                                                                 cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NOnBu                                                                    145                                                                                 ##STR25##                                                                 __________________________________________________________________________

The following o-iminooxymethylbenzoic acid esters V can be prepared, for example, by the processes mentioned.

                                      TABLE 5                                      __________________________________________________________________________      ##STR26##                          V                                          No. R.sup.5 R.sup.4          Data                                              __________________________________________________________________________     1   CN                                                                         2-naphthyl                                                                     2   CN                                                                         n-hexyl                                                                        3   CN                                                                         cyclohexyl                                                                     4   CN                                                                         thiophenyl                                                                     5   CN                                                                         phenyl                                                                         6   CN                                                                         4-Me-phenyl                                                                    7   CN                                                                         4-chlorophenyl                                                                 8   CN                                                                         4-tert-butyl                                                                   9   CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CH.sub.3                                                                   2-naphthyl                                                                     27  CH.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                        IR: 1719; 1261;                                                                                         1136; 1040;                                                                    738 cm.sup.-1                                     32  CH.sub.3                                                                   4-chlorophenyl                                                                     NMR: 2.30(s, 3H);                                                                                       3.90(s, 3H); 5.65                                                              (s, 2H); 8.05-7.25                                                             (m, 8H)                                           33  CH.sub.3                                                                   4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                      47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62  OCH.sub.3                                                                  2-fluorophenyl                                                                 63  OCH.sub.3                                                                  3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub.3                                                                  3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-PrO-phenyl                                                                 86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          99  NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104 SCH.sub.3                                                                  thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NOnBu                                                                    145                                                                                 ##STR27##                                                                 __________________________________________________________________________

The following o-iminooxymethylphenyl ketosulfoxides VII can be prepared, for example, by the processes mentioned.

                                      TABLE 6                                      __________________________________________________________________________      ##STR28##                  VII                                                No. R.sup.5 R.sup.4          Data                                              __________________________________________________________________________     1   CN                                                                         2-naphthyl                                                                     2   CN                                                                         n-hexyl                                                                        3   CN                                                                         cyclohexyl                                                                     4   CN                                                                         thiophenyl                                                                     5   CN                                                                         phenyl                                                                         6   CN                                                                         4-Me-phenyl                                                                    7   CN                                                                         4-chlorophenyl                                                                 8   CN                                                                         4-tert-butyl                                                                   9   CN                                                                         2-MeO-phenyl                                                                   10  CN                                                                         4-i-PrO-phenyl                                                                 11  CN                                                                         2-MeS-phenyl                                                                   12  CN                                                                         2-fluorophenyl                                                                 13  CN                                                                         3-trifluoromethylphenyl                                                        14  CN                                                                         3,5-dichlorophenyl                                                             15  CN                                                                         3-phenylphenyl                                                                 16  CN                                                                         4-phenoxyphenyl                                                                17  CN                                                                         3-CH.sub.3 (CNOMe)-phenyl                                                      18  CN                                                                         3-CH.sub.3 (CNOnBu)-phenyl                                                     19  CN                                                                         3-pyridyl                                                                      20  CN                                                                         5-pyrimidinyl                                                                  21  CN                                                                         3-thienyl                                                                      22  CN                                                                         3-indolyl                                                                      23  CN                                                                         5-(4-methylthiazolyl)                                                          24  CN                                                                         5-indazolyl                                                                    25  CN                                                                         3-(6-chloropyridyl)                                                            26  CH.sub.3                                                                   2-naphthyl                                                                     27  CH.sub.3                                                                   n-hexyl                                                                        28  CH.sub.3                                                                   cyclohexyl                                                                     29  CH.sub.3                                                                   thiophenyl                                                                     30  CH.sub.3                                                                   phenyl                                                                         31  CH.sub.3                                                                   4-Me-phenyl                                                                        IR: 1672; 1038;                                                                                         969; 930; 755 cm.sup.-1                           32  CH.sub.3                                                                   4-chlorophenyl                                                                 33  CH.sub.3                                                                   4-tert-butyl                                                                   34  CH.sub.3                                                                   2-MeO-phenyl                                                                   35  CH.sub.3                                                                   4-i-PrO-phenyl                                                                 36  CH.sub.3                                                                   2-MeS-phenyl                                                                   37  CH.sub.3                                                                   2-fluorophenyl                                                                 38  CH.sub.3                                                                   3-trifluoromethylphenyl                                                        39  CH.sub.3                                                                   3,5-dichlorophenyl                                                             40  CH.sub.3                                                                   3-phenylphenyl                                                                 41  CH.sub.3                                                                   4-phenoxyphenyl                                                                42  CH.sub.3                                                                   3-CH.sub.3 (CNOMe)-phenyl                                                      43  CH.sub.3                                                                   3-CH.sub.3 (CNOnBu)-phenyl                                                     44  CH.sub.3                                                                   3-pyridyl                                                                      45  CH.sub.3                                                                   5-pyrimidinyl                                                                  46  CH.sub.3                                                                   3-thienyl                                                                      47  CH.sub.3                                                                   3-indolyl                                                                      48  CH.sub.3                                                                   5-(4-methylthiazolyl)                                                          49  CH.sub.3                                                                   5-indazolyl                                                                    50  CH.sub.3                                                                   3-(6-chloropyridyl)                                                            51  OCH.sub.3                                                                  2-naphthyl                                                                     52  OCH.sub.3                                                                  n-hexyl                                                                        53  OCH.sub.3                                                                  cyclohexyl                                                                     54  OCH.sub.3                                                                  thiophenyl                                                                     55  OCH.sub.3                                                                  phenyl                                                                         56  OCH.sub.3                                                                  4-Me-phenyl                                                                    57  OCH.sub.3                                                                  4-chlorophenyl                                                                 58  OCH.sub.3                                                                  4-tert-butyl                                                                   59  OCH.sub.3                                                                  2-MeO-phenyl                                                                   60  OCH.sub.3                                                                  4-i-PrO-phenyl                                                                 61  OCH.sub.3                                                                  2-MeS-phenyl                                                                   62  OCH.sub.3                                                                  2-fluorophenyl                                                                 63  OCH.sub.3                                                                  3-trifluoromethylphenyl                                                        64  OCH.sub.3                                                                  3,5-dichlorophenyl                                                             65  OCH.sub.3                                                                  3-phenylphenyl                                                                 66  OCH.sub.3                                                                  4-phenoxyphenyl                                                                67  OCH.sub.3                                                                  3-CH.sub. 3 (CNOMe)-phenyl                                                     68  OCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     69  OCH.sub.3                                                                  3-pyridyl                                                                      70  OCH.sub.3                                                                  5-pyrimidinyl                                                                  71  OCH.sub.3                                                                  3-thienyl                                                                      72  OCH.sub.3                                                                  3-indolyl                                                                      73  OCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          74  OCH.sub.3                                                                  5-indazolyl                                                                    75  OCH.sub.3                                                                  3-(6-chloropyridyl)                                                            76  NHCH.sub.3                                                                 2-naphthyl                                                                     77  NHCH.sub.3                                                                 n-hexyl                                                                        78  NHCH.sub.3                                                                 cyclohexyl                                                                     79  NHCH.sub.3                                                                 thiophenyl                                                                     80  NHCH.sub.3                                                                 phenyl                                                                         81  NHCH.sub.3                                                                 4-Me-phenyl                                                                    82  NHCH.sub.3                                                                 4-chlorophenyl                                                                 83  NHCH.sub.3                                                                 4-tert-butyl                                                                   84  NHCH.sub.3                                                                 2-MeO-phenyl                                                                   85  NHCH.sub.3                                                                 4-i-Pr-o-phenyl                                                                86  NHCH.sub.3                                                                 2-MeS-phenyl                                                                   87  NHCH.sub.3                                                                 2-fluorophenyl                                                                 88  NHCH.sub.3                                                                 3-trifluoromethylphenyl                                                        89  NHCH.sub.3                                                                 3,5-dichlorophenyl                                                             90  NHCH.sub.3                                                                 3-phenylphenyl                                                                 91  NHCH.sub.3                                                                 4-phenoxyphenyl                                                                92  NHCH.sub.3                                                                 3-CH.sub.3 (CNOMe)-phenyl                                                      93  NHCH.sub.3                                                                 3-CH.sub.3 (CNOnBu)-phenyl                                                     94  NHCH.sub.3                                                                 3-pyridyl                                                                      95  NHCH.sub.3                                                                 5-pyrimidinyl                                                                  96  NHCH.sub.3                                                                 3-thienyl                                                                      97  NHCH.sub.3                                                                 3-indolyl                                                                      98  NHCH.sub.3                                                                 5-(4-methylthiazolyl)                                                          99  NHCH.sub.3                                                                 5-indazolyl                                                                    100 NHCH.sub.3                                                                 3-(6-chloropyridyl)                                                            101 SCH.sub.3                                                                  2-naphthyl                                                                     102 SCH.sub.3                                                                  n-hexyl                                                                        103 SCH.sub.3                                                                  cyclohexyl                                                                     104  SCH.sub.3                                                                 thiophenyl                                                                     105 SCH.sub.3                                                                  phenyl                                                                         106 SCH.sub.3                                                                  4-Me-phenyl                                                                    107 SCH.sub.3                                                                  4-chlorophenyl                                                                 108 SCH.sub.3                                                                  4-tert-butyl                                                                   109 SCH.sub.3                                                                  2-MeO-phenyl                                                                   110 SCH.sub.3                                                                  4-i-PrO-phenyl                                                                 111 SCH.sub.3                                                                  2-MeS-phenyl                                                                   112 SCH.sub.3                                                                  2-fluorophenyl                                                                 113 SCH.sub.3                                                                  3-trifluoromethylphenyl                                                        114 SCH.sub.3                                                                  3,5-dichlorophenyl                                                             115 SCH.sub.3                                                                  3-phenylphenyl                                                                 116 SCH.sub.3                                                                  4-phenoxyphenyl                                                                117 SCH.sub.3                                                                  3-CH.sub.3 (CNOMe)-phenyl                                                      118 SCH.sub.3                                                                  3-CH.sub.3 (CNOnBu)-phenyl                                                     119 SCH.sub.3                                                                  3-pyridyl                                                                      120 SCH.sub.3                                                                  5-pyrimidinyl                                                                  121 SCH.sub.3                                                                  3-thienyl                                                                      122 SCH.sub.3                                                                  3-indolyl                                                                      123 SCH.sub.3                                                                  5-(4-methylthiazolyl)                                                          124 SCH.sub.3                                                                  5-indazolyl                                                                    125 SCH.sub.3                                                                  3-(6-chloropyridyl)                                                            126 Me                                                                         2-chlorophenyl                                                                 127 Me                                                                         2-Me-phenyl                                                                    128 Me                                                                         3-chlorophenyl                                                                 129 Me                                                                         3-bromophenyl                                                                  130 Me                                                                         4-nitrophenyl                                                                  131 Me                                                                         tert-butyl                                                                     132 Et                                                                         phenyl                                                                         133 Et                                                                         4-chlorophenyl                                                                 134 Et                                                                         3,5-dichlorophenyl                                                             135 Et                                                                         2-naphthyl                                                                     136                                                                            cyclopropyl                                                                    phenyl                                                                         137                                                                            cyclopropyl                                                                    4-chlorophenyl                                                                 138                                                                            cyclopropyl                                                                    3,5-dichlorophenyl                                                             139                                                                            cyclopropyl                                                                    4-CH.sub.3 O-phenyl                                                            140                                                                            cyclopropyl                                                                    4-tBu-phenyl                                                                   141                                                                            cyclopropyl                                                                    2-naphthyl                                                                     142 CN                                                                         2-chlorophenyl                                                                 143 CN                                                                         2-Me-phenyl                                                                    144 CN                                                                         4-C(H)NOnBu                                                                    145                                                                                 ##STR29##                                                                 __________________________________________________________________________ 

We claim:
 1. An o-iminooxymethyl benzoic acid of the formula I ##STR30## wherein m is an integer from 0 to 3,X is unbranched or branched C₁ -C₄ alkyl; unbranched or branched C₁ -C₄ alkoxy, nitro, cyano or halogen, R¹ is hydrogen; cyano; C₁ -C₆ -alkyl; C₃ -C₆ -cycloalkyl; C₁ -C₄ -alkylthio; C₁ -C₄ -alkylthioalkyl; arylthioalkyl; C₁ -C₄ -alkoxy; C₁ -C₄ -alkoxyalkyl; aryloxyalkyl; C₁ -C₄ alkylamino; C₁ -C₃ -dialkylamino; benzylamino; benzylthio; benzyloxy; benzyl; vinyl; E-chlorovinyl; E-bromovinyl; NH₂ ; --CO-NHCH₃ ; --CONHEt; --CONHnPr; --CONHiPr; --CON(CH₃)₂ ; --CON(Et)₂ ; --COOCH₃ ; --COOEt; --COOnPr; or --COOiPr; R² is C₁ -C₄ -alkyl; phenyl which may be unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkoxy; C₁ -C₄ -alkylthio; fluorine; chlorine; bromine; iodine; C₁ -C₄ -alkyl; C₁ -C₆ -cycloalkyl; nitro; cyano; trifluoromethyl; trichloromethyl; phenyl; phenoxy; benzyl; benzyloxy; C₁ -C₄ -alkylcarbonyl; C₁ -C₄ -alkoxycarbonyl; C₁ -C₄ -alkylaminocarbonyl; C₁ -C₄ -dialkylaminocarbonyl; or C₁ -C₄ -dialkylamino; Ph(Me)N--; Ph(Et)N--; Ph(Et)N--; --SO₂ Me; --SO₂ Et; --SOMe; --SOEt; --SO₂ N(Me)₂ ; --SO₂ N(Et)₂ ; --C(Me)═N--OMe; --C(Me)═N--OEt; --C(Me)═N--OnPr; --C(Me)═N--OiPr; --C(Me)═N--OnBu; --C(Me)═N--OterBu; --C(Me)═N--Obenzyl; --C(Et)═N--OMe; --C(Et)═N--OEt; --C(Et)═N--OnPr; --C(Et) ═N--OiPr; --C(Et)═N--OnBu; --C(Et)═N--OtertBu; --C(Et)═N--Obenzyl; --C(nPr)═N--OMe; --C(nPr)═N--OEt; --C(nPr)═N--OnPr; --C(NPr)═N--OiPr; --C(nPr)═N--OnBu; --C(nPr)═N--OtertBu; --C(nPr)═N-- Obenzyl; --C(iPr)═N--OMe; --C(iPr)═N--OEt; --C(iPr)═OnPr; --C(iPr)═N--OiPr; --C(iPr)═N--OnBu; --C(iPr)═N--OtertBu; --C(iPr)═N--Obenzyl; naphthyl which may be unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkyl; C₁ -C₄ -alkoxy; C₁ -C₄ -alkylthio; F, Cl, Br, NO₂ or CN; phenylcarbonyl, where the phenyl ring can be substituted by 0 to 3 substituents selected from: methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, cyclopropyl, MeO, EtO, nPrO, iPrO, MeS, EtS, F, Cl, Br, I, NO₂, cyano or trifluoromethyl or the radical ##STR31## can have the following meanings ##STR32##
 2. The o-iminooxymethyl benzoic acid compound of claim 1, wherein R¹ is cyano; C₁ -C₆ -alkyl; C₃ -C₆ -cycloalkyl; C₁ -C₄ -alkoxyalkyl; aryloxyalkyl; benzyl; vinyl; E-chlorovinyl; E-bromovinyl; --CO--NHCH₃ ; --CONHEt; --CONHnPr; --CONHiPr; --CON(CH₃)₂ ; --CON(Et)₂ ; --COOCH₃ ; --COOEt; --COOnPr; or --COOiPr;and wherein R² is C₁ -C₄ -alkyl; phenyl which may be unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkoxy; C₁ -C₄ -alkylthio; fluorine; chlorine; bromine; iodine; C₁ -C₄ -alkyl; C₁ -C₆ -cycloalkyl; nitro; cyano; trifluoromethyl; trichloromethyl; phenyl; phenoxy; benzyl; benzyloxy; C₁ -C₄ -alkylcarbonyl; C₁ -C₄ -alkoxycarbonyl; C₁ -C₄ -alkylaminocarbonyl; C₁ -C₄ -dialkylaminocarbonyl; or C₁ -C₄ -dialkylamino; Ph(Me)N--; Ph(Et)N--; Ph(Et)N--; --SO₂ Me; --SO₂ Et; --SOMe; --SOEt; --SO₂ N(Me)₂ ; --SO₂ N(Et)₂ ; --C(Me)═N--OMe; --C(Me)═N--OEt; --C(Me)═N--OnPr; --C(Me)═N--OiPr; --C(Me)═N--OnBu; --C(Me)═N--OterBu; --C(Me)═N--Obenzyl; --C(Et)═N--OMe; --C(Et)═N--OEt; --C(Et)═N--OnPr; --C(Et)═N--OiPr; --C(Et)═N--OnBu; --C(Et)═N--OtertBu; --C(Et)═N--Obenzyl; --C(nPr)═N--OMe; --C(nPr)═N--OEt; --C(nPr)═N--OnPr; --C(NPr)═N--OiPr; --C(nPr)═N--OnBu; --C(nPr)═N--OtertBu; --C(nPr)═N-- Obenzyl; --C(iPr)═N--OMe; --C(iPr)═N--OEt; --C(iPr)═OnPr; --C(iPr)═N--OiPr; --C(iPr)═N--OnBu; --C(iPr)═N--OtertBu; --C(iPr)═N--Obenzyl; naphthyl which may be unsubstituted or substituted by 0 to 3 groups selected from C₁ -C₄ -alkyl; C₁ -C₄ -alkoxy; C₁ -C₄ -alkylthio; F, Cl, Br, NO₂ or CN; or phenylcarbonyl, where the phenyl ring can be substituted by 0 to 3 substituents selected from: methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, cyclopropyl, MeO, EtO, nPrO, iPrO, MeS, EtS, F, Cl, Br, I, NO₂, cyano or trifluoromethyl.
 3. The o-iminooxymethyl benzoic acid of claim 1, wherein m is 0, R¹ is CH₃ and R² is 4--Cl--C₆ H.sub.. 